How to Get Away With Murder Season 3: Why Oliver's Breakup With Connor Confused Us
A release from prison that echoed The Shawshank Redemption, and a split that came at a horrible time
Oliver's decision to step away from Connor in the opening episodes of How to Get Away With Murder season three left us confused, because it seemed to come so suddenly from someone who had been so committed. Before we got to that, though, the story of her release had us talking about what you even do after decades behind bars. We're covering season three three episodes at a time, starting with episodes one, two and three.
Her release from prison played out a lot like The Shawshank Redemption
The story of the woman's release pretty much played out like The Shawshank Redemption. In short, "she abandoned hope of trying to get out" and simply said things as they were. She was very frank about the whole thing, and that's what ultimately set her free.
The difference is that she didn't have any money waiting for her on a beach somewhere or hidden under a brick wall. That would have been a good idea, and the joke was that she needs to go meet a Tim Robbins somewhere.
It brought us back to a question we've talked about before, though neither of us could remember whether it came up with this series or another one: if you've been inside that long, what do you do when you get out? Everybody you knew may be gone. It raised the question of whether there's some kind of support, since sometimes they set you up with a job, like in Shawshank.
A million dollars can't buy back 40 years
That brought to mind a news article from years ago, around 2014 if memory serves, about a man who was wrongfully convicted of murder and sent to prison. DNA evidence later showed he had been wrongfully accused, and he was set free with a million dollars in compensation. The reaction was that it's cool and all, but the man lost 40 years of his life.
We also talked about how risky it could be to hand someone that much money the moment they walk out, without any kind of guidance. You need to be eased into that, and it's hard to know how long the money would last. But the bigger question was whether a million dollars is worth four decades of your life. The answer was simple: "Of course not." Those are years you won't get back, and presumably the best years too, at least as far as mobility goes.
That led to a point we both agreed on: you can always get more money, but you can't get more time. People give up so much time chasing money without realizing that time is the most precious commodity any of us really have.
With her, there was no indication she was given any financial help. The guess was that it might be a thousand dollars, or something like bus money to get somewhere, though what they actually give you had slipped from memory. Without knowing anybody who has had that kind of experience, there was no way to know what happens at that point.
Her husband's abuse was never taken into account
It was hard not to feel awful for her. Her husband was horrible to her, mentally torturing her and basically physically torturing her, and when she finally took action against him, none of his crimes were taken into consideration. She was sent to prison for 30 years, which felt unbelievable.
On top of that, her lawyer told her not to tell anyone about any of the abuse. It's hard to know what the right move would have been back then. If it had happened today, there were laws that would have helped her, so she wouldn't have kept it to herself. For whatever reason, though, he told her to say nothing. Being in prison is like your worst nightmare every day, and the one example she gave of the daily abuse was frightening enough on its own.
So what can you do after something like that? The only move left might be to write a book and share your experience. That brought up the man whose story inspired 127 Hours, who made his profits by telling it. It's a completely different situation, but it was the only comparison that came to mind.
Oliver's sudden need for space seems sad, but you never know what someone is carrying
Moving on to Oliver, the impression was that he's a people pleaser, which is how he describes himself, and he doesn't want to be that anymore. He wants to be on his own and do things for himself. That came across as sad, because the show makes clear his connection with Connor is very strong, and he's risking giving that up for some solo exploration. Isn't there a way to have both and keep growing alongside them? The explanation: "I'm just an optimist."
It also seemed like a quick change. Oliver seemed so all in, and then suddenly he needs time to himself, which was hard to explain.
The counterpoint was that you never know what's going on with somebody in the background. That brought to mind a moment in Scandal where Cyrus talks to Olivia about not being paid attention to, in the context of her and Fitz, though the exact wording was hard to recall. You just never know what's going on in someone's head or what demons they're fighting.
There's a personal example here. When one of our dads passed away, some of his writing was shared at the funeral, and for a lot of people it shed light on who he really was. Most only knew the jovial guy, not the man who was haunted by his childhood and the trauma of an abusive father. So many people were shocked. It's a reminder that sometimes you don't really know who somebody is or what they're dealing with.
Connor changed his life for Oliver, which makes the split confusing
Still, it was easy to feel bad for them. LA is a hard place to date, and if you meet someone you really connect with, maybe you want to figure out a way to hold on to them, because that kind of connection isn't easy to find. So many people are lost on the apps and constantly disappointed. Admittedly, it was a weird case to make for staying together when Oliver is clearly unhappy.
There was also a point about why it's such a confusing situation. Looking at Connor, he didn't want a relationship at all, yet he changed his way of life to be with Oliver, even after Oliver contracted his disease. The Stanford situation kept coming up as a sign of how much was given up so they could be together, which makes Oliver not wanting to be with him now feel strange.
It would be easier to understand if Oliver had asked for a few months to find himself again, and it seems Connor would honestly give it to him. The way Connor is portrayed, it seems like he would be patient and wouldn't look for affection anywhere else. "He feels all in," came the reply. That's why it's perplexing that Oliver didn't ask for a small step instead of a complete severance.
The timing is horrible now that Oliver is working with them
The timing was also horrible. Oliver just started working with the group, so he and Connor are going to see each other all the time. And he's going to be around for a while, because he's now helping cover up what happened. He has to be all in, and they have to trust him.
It's like asking someone to stop being friends with you while they're moving into your apartment to be your roommate. It just feels bizarre. We'll see where it goes from here.
Do you think Oliver was right to ask for time apart from Connor?
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@cinepals · YouTube
Adapted with AI from CinePals' video of 13 October 2026 and reviewed by Digital Fox Talent before publication. Editorial standards · Corrections
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